(S)-5,6-di(nitrooxy)hexanoic acid → (S)-((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl) 5-(nitrooxy)hexanoate

HRID 1676011Notes

Reaction equation

HRID 1676011 reaction equation
[N+]([O:4][C@H:5]([CH2:12][O:13][N+]([O-])=O)[CH2:6][CH2:7][CH2:8][C:9](O)=[O:10])([O-])=O.[N+:17]([O:20][C@@H:21]([CH3:28])[CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])([O-:19])=[O:18]>>[N+:17]([O:20][C@@H:21]([CH3:28])[CH2:22][CH2:23][CH2:24][C:25]([O:27][C@@H:8]1[CH2:9][O:10][C@@H:6]2[C@H:5]([OH:4])[CH2:12][O:13][C@H:7]12)=[O:26])([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 29923588(S)-5,6-di(nitrooxy)hexanoic acidHCID 58231663(S)-5-(nitrooxy)hexanoic acid

Product 1

HCID 59509517(S)-((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl) 5-(nitrooxy)hexanoate

Procedure

The title compound was prepared by following the procedure for the synthesis of EXAMPLE 4, except that in Step F the reagent (S)-5,6-di(nitrooxy)hexanoic acid was replaced by (S)-5-(nitrooxy)hexanoic acid.

Workup

  1. customfor the synthesis of EXAMPLE 4

Sources & evidence

ORD record
ord-088c9d26fc464a70a139f7412db28266
Source dataset
uspto-grants-2011_08
Patent number
US08003811B2

Reaction notes

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